HRID1677430

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21

HCID159087

Triacetoxyperiodinane

C13H13IO8

结构：COc1cc(-c2cnc3c(n2)c(C(O)C2(C)CCN(C(=O)OC(C)(C)C)CC2)cn3[Si](C(C)C)(C(C)C)C(C)C)cc(OC)c1OC

HCID59540603

未命名化合物

PRODUCTS

生成物

HCID14923

Ammonium hydroxide

H5NO

HCID59540581

未命名化合物

结构：COc1cc(-c2cnc3[nH]cc(C(=O)C4(C)CCN(C(=O)OC(C)(C)C)CC4)c3n2)cc(OC)c1OC

HCID59540868

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of 4-{hydroxy-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methyl}-4-methyl-piperidine-1-carboxylic acid tert-butyl ester from above (950 mg, ˜1.4 mmol) in CH2Cl2 (5 mL) was added Dess-Martin periodinane (900 mg, 2.1 mmol) portionwise. The resultant orange suspension was allowed to stir for 1 h and partitioned between 1:1 saturated Na2S2O3:saturated NaHCO3 and CH2Cl2. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4 and concentrated to give a tan solid. The crude product was purified by flash chromatography using 25 g of silica gel and 0-30% of 9.5:0.5 MeOH:conc NH4OH in CH2Cl2 as eluant to afford 150 mg of impure 4-methyl-4-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-piperidine-1-carboxylic acid tert-butyl ester, M+Na 533, and 0.24 g of impure 4-methyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-piperidine-1-carboxylic acid tert-butyl ester, M+Na 689.

WORKUP

后处理

custompartitioned between 1:1 saturated Na2S2O3
extractionThe aqueous phase was extracted with CH2Cl2
dry with materialthe combined organic phases were dried over Na2SO4
concentrationconcentrated
customto give a tan solid
customThe crude product was purified by flash chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2693fa902f554476aed363d3a008d3ae
来源数据集: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08008298B2
来源说明: uspto-grants-2011_08

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:15]([OH:47])[C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=4)[N:23]=3)[N:18]([Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[CH:17]=2)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[NH4+:8].[OH-:5].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([C:15]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([C:25]4[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=4)[N:23]=3)[NH:18][CH:17]=2)=[O:47])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([C:15]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([C:25]4[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=4)[N:23]=3)[N:18]([Si:37]([CH:38]([CH3:40])[CH3:39])([CH:41]([CH3:43])[CH3:42])[CH:44]([CH3:45])[CH3:46])[CH:17]=2)=[O:47])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]